10 Top Chicago Taverns To Mingle When You’re Single


If you already have a date for Valentine’s Day, that’s great. If not, and you’d like one, do something about it. Get out there and meet new people, but don’t be so obvious by hitting up one of those “meet market” madhouses. Instead, be sophisticated about your game and head over to a spot that’s more subtle about its singles scene. From post-work places attracting mature crowds to trivia nights where you can flex your brains instead of muscles, we pick some of our favorite (get a) date bars.

After-Work Action

Henry’s Swing Club (18 W. Hubbard St.). While Hubbard Street’s known as the place to be in River North when you’re on the prowl, this jumpin’ cocktail lounge is a bit of a respite considering its clientele errs on the mature side. It’s a great mix of couples, singles and groups, and the music’s pretty loud, so you’ll have to lean in to talk. You can really break the ice by buying a set of playing cards and seeing who’s game. Uno, anyone?

Pearl Tavern (180 N. Upper Wacker Dr.). With a host of antique and reclaimed accents as well as a mix of classic and contemporary music, Pearl Tavern will make you want to step up your style game. And when you look good, you feel good and confident and so on. With all the law and financial firms in the immediate area, it’s a great place to pop in for oysters, bubbly, and stimulating conversation.

Hot Spots of the Moment

The Betty (839 W. Fulton Market). Just opened this week in the Fulton Market District, The Betty amps up sex appeal in a setting certain not to allow any nonsense. Of course it’s cocktail oriented, featuring enticing elixirs with names like The Ice Breaker (Guatemalan rum, herbal liqueur, creme de menthe) and Maxmillion (tequila, ancho chile liqueur, hibiscus syrup, lime, mole bitters, sparkling wine), so you can check out the beautiful scene as you imbibe. As these places go, it’s certain to attract an A-List local crowd with energy. If nothing else, you’ll at least have fun.

Charlatan (1329 W. Chicago Ave.). This West Town tavern and restaurant opened last fall, but it hasn’t slowed down once–not even on the coldest days in January. For those not dining, the front bar has become quite the hangout for neighborhood types, industry peeps and those looking for action.

Just A Little Taste

CH Distillery (564 W. Randolph St.). The West Loop distillery and bar cranks out signature vodka, gin, rum, limoncello, and more on-premises. But what’s even cooler is that the venue hosts tasting parties and tours on a regular basis. Some events include live music, while others showcase guest bartending sessions by star ‘tenders, and each one is always a learning experience.

Rhine Hall (2010 W. Fulton St.). Interactive classes are always a great way to meet new people, but while classes at this Fulton Market distillery are filled through Valentine’s Day, there’s a chance you may still be able to reserve a spot. No luck? The tasting room and brandy bar are open until 9pm Thursdays and 7pm Saturdays, so you can mix, make new friends and learn everything there’s to know about brandy.

Live Music

City Winery (1200 W. Randolph St.). Live music almost nightly and a great wine program attracts a pretty refined crowd, which is great for you. Grab a few friends and settle into the lounge or bar, or try to get seated at one of the communal tables in the music hall. If you get a good table, does it really matter who’s performing?

Schubas (3159 N. Southport Ave.). This Lakeview tavern is best known for bringing in top Indie bands, but the music hall can get pretty loud. Lucky for you, the bar adjacent to the hall is conversation friendly, so if you meet someone you like, you won’t have to scream. This is a pretty savvy crowd, so know your music.

Trivia Night

Burwood Tap (724 W. Wrightwood Ave.). Got a group of like-minded friends? Bring them to trivia night, happening 9-11pm every Wednesday. It’s $3 per team, plus if you get there around 8:30pm, there’s a complimentary dinner buffet. You know the mind is the sexiest muscle in the body, so go ahead and flex. There are prizes and drink specials, plus Wednesday is one of the busiest nights of the week.

Globe Pub (1934 W. Irving Park Rd.). The brain games begin at 8pm every Tuesday at this rowdy, Euro bar that’s popular with soccer fans. It’s said to be one of the most challenging pub quiz nights in the city, so make sure to sharpen your skills before you arrive.

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The Betty

839 West Fulton Market Chicago IL 60607

(312) 733-2222

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